EP0292761A3 - Pyridoxamine chelating compounds, manganese (ii) chelates and their use as nmri contrast agents - Google Patents

Pyridoxamine chelating compounds, manganese (ii) chelates and their use as nmri contrast agents Download PDF

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Publication number
EP0292761A3
EP0292761A3 EP19880107335 EP88107335A EP0292761A3 EP 0292761 A3 EP0292761 A3 EP 0292761A3 EP 19880107335 EP19880107335 EP 19880107335 EP 88107335 A EP88107335 A EP 88107335A EP 0292761 A3 EP0292761 A3 EP 0292761A3
Authority
EP
European Patent Office
Prior art keywords
pyridoxal
bis
acids
manganese
diacetic
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP19880107335
Other languages
German (de)
French (fr)
Other versions
EP0292761B1 (en
EP0292761A2 (en
Inventor
Scott M. Rocklage
Steven C. Quay
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Amersham Health Salutar Inc
Original Assignee
Nycomed Salutar Inc
Salutar Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nycomed Salutar Inc, Salutar Inc filed Critical Nycomed Salutar Inc
Priority to AT88107335T priority Critical patent/ATE101158T1/en
Publication of EP0292761A2 publication Critical patent/EP0292761A2/en
Publication of EP0292761A3 publication Critical patent/EP0292761A3/en
Application granted granted Critical
Publication of EP0292761B1 publication Critical patent/EP0292761B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/65—One oxygen atom attached in position 3 or 5
    • C07D213/66—One oxygen atom attached in position 3 or 5 having in position 3 an oxygen atom and in each of the positions 4 and 5 a carbon atom bound to an oxygen, sulphur, or nitrogen atom, e.g. pyridoxal
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F13/00—Compounds containing elements of Groups 7 or 17 of the Periodic Table
    • C07F13/005—Compounds without a metal-carbon linkage
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T436/00—Chemistry: analytical and immunological testing
    • Y10T436/24—Nuclear magnetic resonance, electron spin resonance or other spin effects or mass spectrometry

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Radiology & Medical Imaging (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Pyridine Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Manganese(II) chelates of N,N′-bis-(pyridoxal)­ alkylenediamine-N,N′-diacetic acids, N,N′-bis-­ (pyridoxal)-1,2-cycloalkylenediamine-N,N′-diacetic acids, N,N′-bis-(pyridoxal)-1,2-arylenediamine-­ N,N′-diacetic acids, N,N′-bis-(pyridoxal)­ alkylenediamine-N-acetic acids, N,N′-bis-­ (pyridoxal)-1,2-cycloalkylenediamine-N-acetic acids, N,N′-bis-(pyridoxal)-1,2-arylenediamine-N-acetic acids, and their salts are highly stable, superior NMRI contrast agents. They maintain the manganese(II) ion in the +2 valence state. Preferred contrast agents are manganese(II) ion chelates of N,N′-bis-(pyridoxal)ethylenediamine- N,N′-diacetic acid, N,N′-bis-(pyridoxal)trans-1,2-cyclohexylenediamine-­ N,N′-diacetic acid, and the salts and esters thereof.
Novel chelate forming compounds are the N,N′-bis-(pyridoxal)-1,2-cycloalkylenediamine-­ N,N′-diacetic acids and N,N′-bis-(pyridoxal)-1,2-arylene­ diamine-N,N′-diacetic acids, N,N′-bis-(pyridoxal)­ alkylenediamine-N-acetic acids, N,N′-bis(pyridoxal)-­ 1,2-cycloalkylenediamine-N-acetic acids, N,N′-bis-­ (pyridoxal)-1,2-arylenediamine-N-acetic acids, and their salts and esters.
EP88107335A 1987-05-08 1988-05-06 Pyridoxamine chelating compounds, manganese (II) chelates and their use as NMRI contrast agents Expired - Lifetime EP0292761B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT88107335T ATE101158T1 (en) 1987-05-08 1988-05-06 PYRIDOXAMINE CHELATE COMPOUNDS, MANGANESE II CHELATES AND THEIR USE AS NMRI CONTRAST AGENT.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US07/047,584 US4935518A (en) 1987-05-08 1987-05-08 Manganese(II), chelate contrast agents derived from N,N'-bis-(pyridoxal ethylene diamine-N,N')-diacetic acid and derivatives thereof
US47584 1987-05-08

Publications (3)

Publication Number Publication Date
EP0292761A2 EP0292761A2 (en) 1988-11-30
EP0292761A3 true EP0292761A3 (en) 1991-01-30
EP0292761B1 EP0292761B1 (en) 1994-02-02

Family

ID=21949817

Family Applications (1)

Application Number Title Priority Date Filing Date
EP88107335A Expired - Lifetime EP0292761B1 (en) 1987-05-08 1988-05-06 Pyridoxamine chelating compounds, manganese (II) chelates and their use as NMRI contrast agents

Country Status (14)

Country Link
US (1) US4935518A (en)
EP (1) EP0292761B1 (en)
JP (1) JP2773870B2 (en)
AR (1) AR244208A1 (en)
AT (1) ATE101158T1 (en)
CA (1) CA1312867C (en)
DE (1) DE3887566T2 (en)
DK (1) DK251588A (en)
ES (1) ES2061546T3 (en)
FI (1) FI88032C (en)
IE (1) IE63425B1 (en)
IL (1) IL86299A (en)
NO (1) NO174710C (en)
NZ (1) NZ224531A (en)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5250285A (en) * 1985-05-08 1993-10-05 The General Hospital Corporation Hydroxy-aryl metal chelates for diagnostic NMR imaging
US5422096A (en) * 1985-05-08 1995-06-06 The General Hospital Corporation Hydroxy-aryl metal chelates for diagnostic NMR imaging
AR246956A1 (en) 1987-05-08 1994-10-31 Salutar Inc Dipyridoxyl phosphate nuclear magnetic resonance imagery contrast agents
US5130437A (en) * 1987-05-08 1992-07-14 Salutar, Inc. N,N'-bis-(pyridoxal)ethylenediamine-N,N'-diacetic acid derivatives
ES2033433T3 (en) * 1987-07-16 1993-03-16 Nycomed As PROCEDURE TO PREPARE AMINOPOLICARBOXILIC ACIDS AND THEIR DERIVATIVES.
US5531978A (en) * 1987-07-16 1996-07-02 Nycomed Imaging As Aminopolycarboxylic acids and derivatives thereof
US4889931A (en) * 1988-09-27 1989-12-26 Salutar, Inc. Manganese (II) chelate manufacture
US5155224A (en) * 1988-09-27 1992-10-13 Salutar, Inc. Manganese (II) chelates
EP0498380A1 (en) * 1991-02-08 1992-08-12 Byk Gulden Lomberg Chemische Fabrik Gmbh Complexing agents
DE4107570A1 (en) * 1991-03-07 1992-11-19 Diagnostikforschung Inst CHELATES, THEIR METAL COMPLEXES AND THEIR USE IN DIAGNOSTICS AND THERAPY
US5463030A (en) * 1991-05-03 1995-10-31 Research Foundation Of The State Of New York Metal chelating agents for medical application
WO1992021017A1 (en) * 1991-05-23 1992-11-26 Unger Evan C Liposoluble compounds for magnetic resonance imaging
US5385719A (en) * 1991-09-24 1995-01-31 Unger; Evan C. Copolymers and their use as contrast agents in magnetic resonance imaging and in other applications
EP0648209A1 (en) * 1992-07-01 1995-04-19 Byk Gulden Lomberg Chemische Fabrik GmbH Contrast agents for mr diagnosis
US5364953A (en) * 1992-11-05 1994-11-15 Mallinckrodt Medical, Inc. High relaxivity, paramagnetic, metal clusters for magnetic resonance imaging
US5330743A (en) * 1992-11-12 1994-07-19 Magnetic Research, Inc. Aminosaccharide contrast agents for magnetic resonance images
US5582814A (en) * 1994-04-15 1996-12-10 Metasyn, Inc. 1-(p-n-butylbenzyl) DTPA for magnetic resonance imaging
TW319763B (en) 1995-02-01 1997-11-11 Epix Medical Inc
GB9613182D0 (en) * 1996-06-24 1996-08-28 Nycomed Imaging As Method
GB9727224D0 (en) * 1997-12-23 1998-02-25 Nycomed Imaging As Method
ATE277038T1 (en) * 1997-12-23 2004-10-15 Amersham Health As NITROGEN OXIDE RELEASING CHELATING AGENTS AND THEIR THERAPEUTIC USE
GB2333704A (en) * 1998-01-31 1999-08-04 Procter & Gamble Contrasting compositions for magnetic resonance imaging comprising a complex of ethylene diamine disuccinic acid and one or more paramagnetic metal ions
WO2010133907A1 (en) * 2009-05-18 2010-11-25 Carlo Ghisalberti Hexadentate chelators in inflammatory bowel disease
US20150313921A1 (en) * 2012-11-02 2015-11-05 Pledpharma Ab Cancer Treatment Methods

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4322361A (en) * 1980-03-03 1982-03-30 The Dow Chemical Company Method of preparing a manganese chelate having improved properties
WO1985005554A1 (en) * 1984-05-31 1985-12-19 Amersham International Plc Nmr contrast agents

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4322361A (en) * 1980-03-03 1982-03-30 The Dow Chemical Company Method of preparing a manganese chelate having improved properties
WO1985005554A1 (en) * 1984-05-31 1985-12-19 Amersham International Plc Nmr contrast agents

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
INT. J. NUCL. MED. BIOL. vol. 12, no. 5, 1985, pages 381-386; M.A. GREEN et al.: "Evaluation of PLED as a Chelating ligand for the Preparation of Gallium and Indium Radiopharmaceuticals" *

Also Published As

Publication number Publication date
JPS63287791A (en) 1988-11-24
US4935518A (en) 1990-06-19
DK251588A (en) 1988-11-09
FI88032C (en) 1993-03-25
DE3887566D1 (en) 1994-03-17
ATE101158T1 (en) 1994-02-15
NO174710C (en) 1994-06-22
FI882126A (en) 1988-11-09
AU1568188A (en) 1989-11-09
FI88032B (en) 1992-12-15
EP0292761B1 (en) 1994-02-02
IL86299A (en) 1993-01-14
NZ224531A (en) 1993-05-26
IE881367L (en) 1988-11-08
NO882003D0 (en) 1988-05-06
NO882003L (en) 1988-11-09
AU612647B2 (en) 1991-07-18
CA1312867C (en) 1993-01-19
JP2773870B2 (en) 1998-07-09
AR244208A1 (en) 1993-10-29
FI882126A0 (en) 1988-05-06
DE3887566T2 (en) 1994-05-11
ES2061546T3 (en) 1994-12-16
IL86299A0 (en) 1988-11-15
EP0292761A2 (en) 1988-11-30
DK251588D0 (en) 1988-05-06
IE63425B1 (en) 1995-04-19
NO174710B (en) 1994-03-14

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